56139-59-4

Upstream product

• 3240-29-7 1-Phenylpent-4-en-1-one 
• 64-19-7 acetic acid 
• 96183-53-8 4,4-Dimethoxy-1-phenyl-1-butanone 
• 117203-21-1 1-(formyloxy)-4-methoxy-4-phenyl-1(Z),3-butadiene 
• 28531-58-0 (2-oxo-2-phenylethyl)mercury chloride 
• 109-92-2 ethyl vinyl ether 
• 131684-96-3 1-(2,2-dimethylpropanoyl)-5-ethoxy-1-azacyclopentanone 
• 2051-95-8 succinylbenzene 
• 622860-41-7 trans-1,5-diphenyl-4-penten-1-ol 
• 4850-50-4 1-phenyl-butane-1,4-diol 
• 4535-44-8 (E)-1-phenylhex-4-ene-1-ol 
• 102632-99-5 1-phenyl-4-penten-1-ol 
• 3365-26-2 1-phenylcyclobutene 
• 98-88-4 benzoyl chloride 

Downstream Products

• 4850-50-4 1-phenyl-butane-1,4-diol 
• 124851-55-4 (1S,5R)-3-Oxo-1-phenyl-8-oxa-bicyclo[3.2.1]octane-2-carboxylic acid methyl ester 
• 124851-67-8 2-(methoxycarbonyl)-5-phenyl-8-oxabicyclo<3.2.1>octan-3-one 
• 3042-22-6 2-phenyl-1H-pyrrole 
• 98-86-2 acetophenone 
• 2051-95-8 succinylbenzene 
• 849771-48-8 (S)-2-dibenzylamino-4-(2-phenylpyrrol-1-yl)butan-1-ol 
• 158883-32-0 2-(2-phenyl-1H-pyrrol-1-yl)isoindoline-1,3-dione 

Relevant academic research and scientific papers

From Ring-Expansion to Ring-Contraction: Synthesis of γ-Lactones from Cyclobutanols and Relative Stability of Five- and Six-Membered Endoperoxides toward Organic Bases

Cyclobutanols undergo ring expansion with molecular oxygen in the presence of Co(acac)2 to afford 1,2-dioxane-hemiperoxyketals. In the course of acylation, we observed that endoperoxides rearranged into ?-lactone in the presence of triethylamine. Thus, a generalization of this ring contraction through a Kornblum DeLaMare rearrangement is here reported. Application of this transformation to monosubstituted 1,2-dioxane derivatives also led to 1,4-ketoaldehydes, in proportions depending on the nature of the substituent. These same conditions applied to five-membered dioxolane analogues led to fragmentation instead, through a retro-aldol type process. This study emphasizes the difference of stability of 1,2-dioxane and 1,2-dioxolane against organic bases, 1,2-dioxolanes having proved to be particularly reactive whereas 1,2-dioxanes showed a relative tolerance under these conditions.

VISIBLE-LIGHT MEDIATED ORGANOPHOTOREDOX CATALYTIC DEUTERATION OF AROMATIC AND ALIPHATIC ALDEHYDES

Described are methods for preparing a deuterated aldehyde using with a photocatalyst and a hydrogen atom transfer agent in a H2O free solvent comprising D2O and an organic solvent under an inert gas. The methods may be used to convert a wide variety of aldehydes (e.g., aryl, alkyl, or alkenyl aldehydes) to C-1 deuterated aldehydes under mild reaction conditions.

Dibromo-BODIPY as an Organic Photocatalyst for Radical-Ionic Sequences

A new dibrominated 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) is reported as a new metal-free photocatalyst. This BODIPY showed similar optoelectronic, electrochemical, and performance properties to those of Ru(bpy)3Cl2, one of the most common photocatalysts in a known radical-ionic transformation, such as the formation of 1,4-dicarbonyl compounds. Moreover, additional sequences in which the generated oxonium ion is trapped by an internal nucleophile were developed using this BODIPY photocatalyst. These new sequences allowed the straightforward preparation of ?3-alkoxylactones, monoprotected 1,4-ketoaldehydes, and dihydrofurans. This new catalyst, the methodology, and the forged functional groups could be important tools in organic synthesis.

Atroposelective Synthesis of Axially Chiral N-Arylpyrroles by Chiral-at-Rhodium Catalysis

A transformation of fluxional into configurationally stable axially chiral N-arylpyrroles was achieved with a highly atroposelective electrophilic aromatic substitution catalyzed by a chiral-at-metal rhodium Lewis acid. Specifically, N-arylpyrroles were alkylated with N-acryloyl-1H-pyrazole electrophiles in up to 93 percent yield and with up to >99.5 percent ee, and follow-up conversions reveal the synthetic utility of this new method. DFT calculations elucidate the origins of the observed excellent atroposelectivity.

Sequential multicomponent catalytic synthesis of pyrrole-3-carboxaldehydes: Evaluation of antibacterial and antifungal activities along with docking studies

A sequential multicomponent synthesis of highly substituted pyrrole-3-carboxaldehydes has been developed under metal-free conditions. This one-pot protocol involves proline-catalyzed direct chemoselective Mannich reaction-cyclization between 1,4-ketoaldehyde and in situ generated Ar/HetAr-imines followed by aerobic oxidative-aromatization at room temperature. A series of fully substituted pyrrole-3-carboxaldehydes and other diverse fused heterocycles have been synthesized. These compounds were tested for in vitro antibacterial and antifungal activities, and the selected ones display significant activity against the tested bacterial strains with a MIC value of 16 μg mL-1, which is close to that of the standard drug chloramphenicol. The bioactivity outcome was further analyzed using docking studies.

Photo-organocatalytic synthesis of acetals from aldehydes

A mild and green photo-organocatalytic protocol for the highly efficient acetalization of aldehydes has been developed. Utilizing thioxanthenone as the photocatalyst and inexpensive household lamps as the light source, a variety of aromatic and aliphatic aldehydes have been converted into acyclic and cyclic acetals in high yields. The reaction mechanism was extensively studied.

Visible-Light Photocatalytic Preparation of 1,4-Ketoaldehydes and 1,4-Diketones from α-Bromoketones and Alkyl Enol Ethers

A Ru2+-photocatalyzed, visible-light-mediated ATRA reaction for the straightforward preparation of 1,4-ketoaldehydes, 1,4-diketones, and 1,4-ketoesters, which are of difficult access by other means, is reported herein. This method employs readily accessible α-bromoketones and alkyl vinyl ethers as starting materials, allowing the construction of secondary, tertiary, and challenging quaternary centers. In addition, the synthetic usefulness of this method is illustrated by applying it to the construction of substituted pyrroles.

Continuous Endoperoxidation of Conjugated Dienes and Subsequent Rearrangements Leading to C-H Oxidized Synthons

We have investigated the continuous flow photooxidation of several conjugated dienes and subsequent rearrangement using a practical and safe continuous-flow homemade engineered setup. End-to-end approaches involving endoperoxidation, Kornblum-DeLaMare rearrangement, and additional rearrangements are comprehensively detailed with optimization, scope, and scale-up to obtain useful hydroxyenones, furans, and 1,4-dicarbonyl building blocks.

Visible-Light-Promoted Synthesis of 1,4-Dicarbonyl Compounds via Conjugate Addition of Aroyl Chlorides

A facile visible-light photocatalytic conjugate addition to prepare 1,4-dicarbonyl compounds has been developed by employing readily available aroyl chlorides as aryl radical sources. This operationally simple method shows a broad scope with regard to both aroyl chlorides and Michael acceptors. As a result, a variety of 1,4-diketones were efficiently synthesized in moderate to good yields.

Organocatalytic Redox Isomerization of Electron-Deficient Allylic Alcohols: Synthesis of 1,4-Ketoaldehydes

An organocatalytic redox isomerization strategy has been developed for the synthesis of 1,4-ketoaldehydes. DABCO was found to be the best catalyst for the isomerization of -hydroxy enones. With 20 mol % of DABCO as catalyst and DMSO as the solvent high yi